[(2R,3R,4R,5R)-5-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate -Drug Synthesis Database

【结构式】

【分子编号】41251

【品名】[(2R,3R,4R,5R)-5-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate

【CA登记号】

【分子式】C₃₁H₂₄IN₅O₇

【分子量】705.46553

【元素组成】C 52.78% H 3.43% I 17.99% N 9.93% O 15.88%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The iodination of 1H-pyrazolo[3,4-d]pyrimidine-4-amine (I) with N-yodosuccinimide (NIS) gives 3-iodo-1H-pyrazolo[3,4-d]pyrimidine-4-amine (II), which is condensed with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (III) by means of BF3/ethyl ether in nitromethane to yield the benzoylated adduct (IV). Finally this compound is deprotected with sodium methoxide.

参考文献中间体

合成目标

【1】 Robins, R.K.; Potential purine antagonists. I. Synthesis of some 4,6-substituted pyrazolo[3,4-d]pyrimidines. J Am Chem Soc 1956, 78, 784-790.
【2】 Cottam, H.B.; New adenosine kinase inhibitors with oral antiinflammatory activity. Drugs Fut 1994, 19, 5, 485.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	41249	4-amine-1H-pyrazolo[3,4-d]pyrimidine; 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine; 1H-pyrazolo[3,4-d]pyrimidin-4-amine	2380-63-4	C₅H₅N₅	详情	详情
(II)	41250	3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine		C₅H₄IN₅	详情	详情
(III)	26984	(2R,3R,4R,5S)-5-(acetoxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]tetrahydro-3-furanyl benzoate		C₂₈H₂₄O₉	详情	详情
(IV)	41251	[(2R,3R,4R,5R)-5-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate		C₃₁H₂₄IN₅O₇	详情	详情

Extended Information